NP-MRD: Showing NP-Card for (+)-11,11'-Dideoxyverticillin A (NP0068850)

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Record Information

Version

2.0

Created at

2022-04-28 14:06:19 UTC

Updated at

2022-04-28 14:06:19 UTC

NP-MRD ID

NP0068850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-11,11'-Dideoxyverticillin A

Description

11,11'-Dideoxyverticillin A, also known as verticillins, belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (+)-11,11'-Dideoxyverticillin A is found in Penicillium sp. (+)-11,11'-Dideoxyverticillin A was first documented in 2009 (PMID: 19847339). Based on a literature review very few articles have been published on 11,11'-Dideoxyverticillin A (PMID: 19359584).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216062D          

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M  END

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M  END


  Mrv1652304282216062D          

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    4.8712    1.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6994    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2689    1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560    1.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    1.4917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974    0.7786    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5765    2.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641    1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3504   -0.3603    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0952   -1.0733    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4385   -1.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  5  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 10 19  1  6  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  6  0  0  0
 29 28  1  1  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 21 38  1  0  0  0  0
 25 39  1  1  0  0  0
 24 40  1  0  0  0  0
  6 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
  2 43  1  1  0  0  0
  1 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@@]23C[C@]4([C@H](NC5=C4C=CC=C5)N2C(=O)[C@]1(C)SS3)[C@]12C[C@]34SS[C@](C)(N(C)C3=O)C(=O)N4[C@H]1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H28N6O4S4/c1-25-21(37)35-19-27(15-9-5-7-11-17(15)31-19,13-29(35,43-41-25)23(39)33(25)3)28-14-30-24(40)34(4)26(2,42-44-30)22(38)36(30)20(28)32-18-12-8-6-10-16(18)28/h5-12,19-20,31-32H,13-14H2,1-4H3/t19-,20-,25+,26+,27+,28+,29+,30+/m1/s1

> <INCHI_KEY>
PVVLIIZIQXDFSP-PNVYSBBASA-N

> <FORMULA>
C30H28N6O4S4

> <MOLECULAR_WEIGHT>
664.83

> <EXACT_MASS>
664.105488102

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
65.09397025381793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,11R,14S)-3-[(1S,3R,11R,14S)-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.673004038666666

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.076103166718507

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.076103166718507

> <JCHEM_PKA_STRONGEST_BASIC>
2.333132954706449

> <JCHEM_POLAR_SURFACE_AREA>
105.29999999999998

> <JCHEM_REFRACTIVITY>
174.84839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,11R,14S)-3-[(1S,3R,11R,14S)-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0      13.190  -0.885   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      12.740  -2.500   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.149  -3.131   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.788  -4.628   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      10.008  -1.826   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.474  -0.172   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.097   0.437   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.493   1.925   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.064   0.573   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.782  -0.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.408  -1.737   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.263  -2.768   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.930  -1.997   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.250  -0.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.106   0.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.641   0.065   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.321  -1.442   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.465  -2.472   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.241   1.111   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.959   0.208   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.548   0.953   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.926   0.344   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.213  -1.220   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       1.833   1.666   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.283   3.281   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.873   3.912   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.867   5.541   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       5.014   2.607   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       6.615   2.518   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       7.760   3.548   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       9.093   2.778   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.772   1.272   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.916   0.241   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.381   0.716   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.702   2.222   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.558   3.253   0.000  0.00  0.00           C+0
HETATM   37  S   UNK     0       3.645   2.784   0.000  0.00  0.00           S+0
HETATM   38  S   UNK     0       3.169   1.453   0.000  0.00  0.00           S+0
HETATM   39  C   UNK     0       1.076   4.425   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.120   1.898   0.000  0.00  0.00           C+0
HETATM   41  S   UNK     0      11.854  -0.672   0.000  0.00  0.00           S+0
HETATM   42  S   UNK     0      11.378  -2.004   0.000  0.00  0.00           S+0
HETATM   43  C   UNK     0      13.885  -3.530   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.696  -0.565   0.000  0.00  0.00           C+0
CONECT    1    2    7   44                                                  
CONECT    2    1    3   42   43                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    9   41                                             
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   14   19                                             
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   10   20   29   32                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   28   38                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   40                                                  
CONECT   25   24   26   37   39                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28   19   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   19   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   25   38                                                       
CONECT   38   37   21                                                       
CONECT   39   25                                                            
CONECT   40   24                                                            
CONECT   41    6   42                                                       
CONECT   42   41    2                                                       
CONECT   43    2                                                            
CONECT   44    1                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  106    0
END

View in JSmol

Synonyms

Value	Source
11'-Deoxyverticillin a	MeSH
Verticillin a	MeSH
Verticillins	MeSH

Chemical Formula

C₃₀H₂₈N₆O₄S₄

Average Mass

664.8300 Da

Monoisotopic Mass

664.10549 Da

IUPAC Name

(1S,3R,11R,14S)-3-[(1S,3R,11R,14S)-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@@]23C[C@]4([C@H](NC5=C4C=CC=C5)N2C(=O)[C@]1(C)SS3)[C@]12C[C@]34SS[C@](C)(N(C)C3=O)C(=O)N4[C@H]1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C30H28N6O4S4/c1-25-21(37)35-19-27(15-9-5-7-11-17(15)31-19,13-29(35,43-41-25)23(39)33(25)3)28-14-30-24(40)34(4)26(2,42-44-30)22(38)36(30)20(28)32-18-12-8-6-10-16(18)28/h5-12,19-20,31-32H,13-14H2,1-4H3/t19-,20-,25+,26+,27+,28+,29+,30+/m1/s1

InChI Key

PVVLIIZIQXDFSP-PNVYSBBASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Epipolythiodioxopiperazine
Indole
Dihydroindole
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-methylpiperazine
N-alkylpiperazine
Benzenoid
Piperazine
1,4-diazinane
Dithiazinane
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Carboxamide group
Organic disulfide
Lactam
Azacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.67	ALOGPS
logP	3.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.08	ChemAxon
pKa (Strongest Basic)	2.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	174.85 m³·mol⁻¹	ChemAxon
Polarizability	65.09 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026933

Chemspider ID

2341238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084126

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim J, Movassaghi M: Biogenetically inspired syntheses of alkaloid natural products. Chem Soc Rev. 2009 Nov;38(11):3035-50. doi: 10.1039/b819925f. Epub 2009 Sep 23. [PubMed:19847339 ]
Kim J, Ashenhurst JA, Movassaghi M: Total synthesis of (+)-11,11'-dideoxyverticillin A. Science. 2009 Apr 10;324(5924):238-41. doi: 10.1126/science.1170777. [PubMed:19359584 ]

Showing NP-Card for (+)-11,11'-Dideoxyverticillin A (NP0068850)

MOL for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

3D MOL for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

3D SDF for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

3D-SDF for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

PDB for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

3D PDB for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

SMILES for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

INCHI for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

Structure for NP0068850 ((+)-11,11'-Dideoxyverticillin A)

3D Structure for NP0068850 ((+)-11,11'-Dideoxyverticillin A)